N-alkylated iminoketones.



s ra rns KURT HESS, 0F LEVERKUSEN, NEAR COLOGNE. GERMANY, ASSIGNGR TO SYNTHETIC PATENTS CO., INC, OF NEW YORK, N. Y., A CORPORATION OF NEW YUHK.

N-ALKYLATED IMINOKETONES.

1,158A9fi.

No Drawing.

1 '0 all whom it may concern Be it known that I, KURT 'Hnss, doctor of philosophy, chemist, citizen of the German Empire, residing at Leverkusen, near Cologne, Germany, have invented new and useful Improvements in NAlkylated Iminoketones, of which the following is a specification.

I have found that new and valuable products can be obtained from organic substances containing an oxidizable group and containing nitrogen linked together withhydrogen replaceable by an alkyl, such as a heterocyclic imino alcohol containing an exocyclic carbinol group, by heating them with an aldehvde e. g. formic aldehyde or benzaldehyde. By this operation oxidation and alkylation takes place at the same time, the parent material being converted into an aminoketone. The new products are generally oils of an alkaline reaction generally soluble in water, alcohol and ether; yielding crystalline picrates and oxims.

In order to illustrate the new process more fully the following example is given, the parts being by weight: 560 parts of alphapyrrolidylpropan- (-1-)ol having most prob ably the formula:

UHF-CH5 are. dissolved in 1000 parts of water. Concentrated hydrochloric acid is added to N la,

is precipitated by the addition iii-alkali and dissolved by shaking the mixturewith ether.

-It is an oil of a disagreeable basic odor easily Specification of Letters Patent.

,water, alcohol and ether,

acidulate the solution and the liquid is heatfiltllfylfittl'bmljvl 1 olymethyleneimins generally oils of an alkaline reaction gene i Patented Elev. 23, 10ft Application filed (lctober Q, 1914. Serial No. 855,300.

soluble in water and the usual organic sol- ,vents. it boils at 7075 (l under a pressure of 1:5 mm. Its picrate melts at 103 C. From the isomeric alpha-pyrrolidvlpropan- (2-)ol having most probably tlie tormulat eta-Ana2 QHz cn on-oHon-ctn an oil having most probably the formula CHg CI'Iz onz cn-om-co-cn3 nine reaction generahy soluble in vieloin crystalline picrates and calms, substantially as described.

2. The herein described new n-alkyi-c-allzylcarbonyl-polymethyleneimias being generally oils of an alkaline reaction generally soluble in water, alcohol, and ether; ieldin g crystalline picrates and oxims, substantially as described.

3. The herein described new n-inethyl-c-alkylcarhonyl-polyn'iethyleneimins being generally oils ot an alkaline reaction generally soluble in water, alcohol and ether yielding crystalline pier-ates and orzims, substantially as described.

4. The herein described new nall yl-cbeing ally soluble in water, alcohol and ether; yielding crystalline picrates and oxims, stantially as described.

5. The herein described alpha-nrmethyl pyrrolidvlpropan- -1-) -onhaving most pinbably the formula: v

CHz---0Hg being an oil of a disagreeable basic odor ganic solvents; boiling at from 70 4' C.

under a pressure of 12 nmr; its picmte melt.

my hand in the presence 01? two su'l.=s :ribing witnesses.

KURT HESS. Wifinesses A. H. Scmmmm, M. J. SPALDING. 

